CN112220962A - Medical adhesive material capable of rapidly stopping bleeding and preparation method thereof - Google Patents
Medical adhesive material capable of rapidly stopping bleeding and preparation method thereof Download PDFInfo
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- CN112220962A CN112220962A CN202011197506.8A CN202011197506A CN112220962A CN 112220962 A CN112220962 A CN 112220962A CN 202011197506 A CN202011197506 A CN 202011197506A CN 112220962 A CN112220962 A CN 112220962A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/08—Polysaccharides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/001—Use of materials characterised by their function or physical properties
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/06—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/04—Materials for stopping bleeding
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- Surgery (AREA)
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Materials For Medical Uses (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention belongs to the technical field of biomedical materials, and particularly relates to a medical adhesive material for rapidly stopping bleeding, and further discloses a preparation method of the medical adhesive material. The medical adhesive material of the invention takes alpha-n-butyl cyanoacrylate and alpha-n-octyl cyanoacrylate as mixed medical adhesive matrix and CO2The supercritical fluid carries the selected ionic liquid to carry out swelling modification on the hemostatic material carboxymethyl chitosan, so that the hemostatic performance of the carboxymethyl chitosan is effectively improved, the hemostatic performance of the whole medical adhesive material is greatly improved, and rapid hemostasis is realized.
Description
Technical Field
The invention belongs to the technical field of biomedical materials, and particularly relates to a medical adhesive material for rapidly stopping bleeding, and further discloses a preparation method of the medical adhesive material.
Background
The medical adhesive is a preparation, a material or a substance which can be adhered to the surface or can cause the surface to be adhered in the aspect of medical treatment, belongs to biomedical special functional adhesive, is mainly used for local adhesion and repair of organs or tissues, replaces the technical fields of traditional suturing, or combination and positioning of tissues and blood vessels for plugging and the like, and has the biomedical function besides the common adhesive bonding function and the mechanical function. Compared with the traditional methods such as suturing and nailing, the use of the medical adhesive can effectively shorten the operation time and obviously reduce the pain of patients, and is the preferred material for the current medical operation.
Currently, cyanoacrylate medical adhesives have been rapidly developed and widely used clinically in recent decades. Structure CNCH of cyanoacrylate medical glue2In CCOOR, alpha-carbon atom is combined with-CN, -COOR group, so that the carbon atom at beta position generates stronger electroabsorbability, and only a very trace amount of anions (-OH, -NH) are met2) I.e., instantaneously polymerize. Because the basic substance of the organism tissue is protein, the protein is a linear macromolecular compound consisting of amino acid, and the two ends of the macromolecule contain-NH2and-COOH group, the cyanoacrylate medical adhesive has the fastest polymerization speed on organism tissues and obvious performance advantage.
In addition, when the cyanoacrylate medical adhesive is used on biological tissues, due to the existence of trace alkalescent materials such as tissue fluid, water or blood and the like on the biological tissues, the cyanoacrylate monomer can be rapidly initiated to generate anionic polymerization at room temperature, and then the alpha-cyanoacrylate monomer is solidified into an adhesive film, the adhesive film is scanned under an electron microscope to form a polymer with a 2-3 micron fiber mesh structure, and the adhesive film is tightly embedded with the skin surface, the surgical wound surface, the medical material surface and the like, so that the adhesive can be used for bonding and closing the wound, sealing the small blood vessel mesh of the wound surface fracture to effectively seal and stop bleeding, bonding and fixing autologous tissues and medical materials, and plugging/sealing blood vessels.
However, even though the prior art has developed a cyanoacrylate medical adhesive formed by compounding different cyanoacrylate materials, the adhesive property of the cyanoacrylate medical adhesive is further improved. However, with the increasingly wide application range of medical glue, there is a clinical urgent need for medical glue materials with both hemostatic and adhesive properties to meet the needs of different medical conditions, but the hemostatic properties of pure cyanoacrylate medical glue materials are very limited, and clinical needs cannot be met.
Disclosure of Invention
Therefore, the technical problem to be solved by the invention is to provide a medical adhesive material capable of rapidly stopping bleeding, so as to solve the problem that the pure cyanoacrylate medical adhesive material in the prior art has poor hemostatic performance;
the second technical problem to be solved by the present invention is to provide a method for preparing the medical adhesive material for rapid hemostasis.
In order to solve the technical problems, the preparation method of the medical adhesive material for rapidly stopping bleeding provided by the invention comprises the following steps:
(1) uniformly mixing alpha-n-butyl cyanoacrylate and alpha-n-octyl cyanoacrylate to obtain a medical adhesive matrix for later use;
(2) placing carboxymethyl chitosan in a sealed container filled with ionic liquid, removing air, and charging CO into the container2Controlling the temperature and pressure in the closed container to make CO2The gas is in a supercritical state, and carries the ionic liquid to modify the carboxymethyl chitosan under the condition that the carboxymethyl chitosan is not in contact with the ionic liquid, so as to obtain the carboxymethyl chitosan to be modified, and the carboxymethyl chitosan is dried for standby;
(3) slowly adding the modified carboxymethyl chitosan into the medical gel matrix, fully stirring until the system is in a gel state, and sterilizing to obtain the medical gel matrix.
Specifically, in the step (1), the mass ratio of the n-butyl alpha-cyanoacrylate to the n-octyl alpha-cyanoacrylate is 50-60 wt%: 40-50 wt%.
Specifically, in the step (2), the ionic liquid comprises 1-methylimidazole trifluoroacetate.
Specifically, in the step (2), the addition amount of the ionic liquid accounts for 5-10 wt% of the mass of the carboxymethyl chitosan.
Specifically, in the step (2), the temperature in the closed container is controlled to be 80-120 ℃ and the pressure is controlled to be 8-10 MP.
Specifically, in the step (2), the time of the modification treatment step is 5-10 min.
Specifically, in the step (3), the mass ratio of the modified carboxymethyl chitosan to the medical gum base is 3-8: 10.
specifically, the step (3) further comprises a step of adding a functional auxiliary agent.
The invention also discloses a medical adhesive material for rapid hemostasis prepared by the method.
The invention also discloses application of the medical adhesive material for rapidly stopping bleeding in preparation of a hemostatic material.
The medical adhesive material of the invention takes alpha-n-butyl cyanoacrylate and alpha-n-octyl cyanoacrylate as mixed medical adhesive matrix and CO2The supercritical fluid carries the selected ionic liquid to carry out swelling modification on the hemostatic material carboxymethyl chitosan, so that the hemostatic performance of the carboxymethyl chitosan is effectively improved, the hemostatic performance of the whole medical adhesive material is greatly improved, and rapid hemostasis is realized.
Detailed Description
Preparation example 1 preparation of n-butyl alpha-cyanoacrylate
The preparation example is used for preparing the required alpha-n-butyl cyanoacrylate, and specifically comprises the following steps:
(1) transesterification of butyl esters
CNCH2COOC2H5+C4H9OH—C2H5ONa→CNCH2COOC4H9+C2H5OH
Putting 1400ml of ethyl cyanoacetate and 1200ml of n-butanol into a 5L three-mouth beaker provided with a stirrer and a thermometer, starting stirring, condensing water, heating to 40 ℃ or above, and adding 25g of sodium ethoxide; heating to 100 deg.C, distilling off ethanol when the top temperature reaches 78-82 deg.C, stopping heating when the internal temperature reaches 110 deg.C and the top temperature reaches 98-100 deg.C, and recovering about 680ml ethanol;
cooling to about 50 ℃ of internal temperature, starting a heating and vacuum pump, changing bottles to receive n-butyl cyanoacetate when the vacuum degree is-0.1 MPa and the internal temperature is raised to about 95 ℃ and the top temperature is about 80 ℃, and receiving about 80g of n-butyl cyanoacetate when the bottles are changed; when the internal temperature reaches 130 ℃ and the top temperature reaches 100-;
(2) cracking formaldehyde
【CH2O】n-CH3OH→n CH2O+CH3OH
Putting 3000ml of methanol, 1000g of formaldehyde and 1ml of piperidine into a 5L three-mouth beaker, and cracking solid formaldehyde into monomer formaldehyde, namely methanol formaldehyde solution, under the conditions of micro-heating, reflux and stirring;
(3) synthesis of n-butyl alpha-cyanoacrylate
Adding 790ml of methanol formaldehyde solution and 2.1ml of piperidine into a 5L three-neck flask provided with a stirrer, a dropping funnel, a condenser and a water separator, starting to dropwise add 1000ml of n-butyl cyanoacetate when the temperature in the flask reaches 40 ℃ or above, and collecting methanol until the internal temperature reaches 110 ℃; then 400ml of petroleum ether is dripped to begin dehydration and accelerate stirring, about 32ml of water is actually collected after the ether water in the reflux water separator is layered and clarified, and about 400ml of petroleum ether is collected after the water is collected; when the internal temperature reaches 125 ℃, adding 28g of phosphorus pentoxide and 1g of hydroquinone, accelerating the uniform stirring, simultaneously removing the stirrer, the water separator and the dropping funnel, inserting the thermometer and the receiving pipe, connecting the stirrer, the water separator and the dropping funnel with the straight condenser, starting the vacuum pump, removing low-boiling-point substances, continuously adjusting the vacuum degree, changing the receiving bottle when the internal temperature is raised to 140 ℃ after the stirring is stable, and collecting the butyl ester crude monomer when the internal temperature is 160-.
(4) Rectification of n-butyl alpha-cyanoacrylate
A2L two-mouth flask (containing coarse monomer) is provided with an air pipe, a fractionating head, a direct type condenser and a receiving bottle, pressure is reduced, when the vacuum temperature reaches-0.1 MPa or below, the temperature is rapidly increased, when the internal temperature is 95-170 ℃, the rectification monomer is discharged, an air release valve is opened, pressure is increased, a product is taken down and weighed, and then sampling is carried out for chemical analysis.
This preparation was tested to yield the desired n-butyl α -cyanoacrylate.
Preparation example 2 preparation of n-octyl alpha-cyanoacrylate
The preparation example is used for preparing the required n-octyl alpha-cyanoacrylate, and specifically comprises the following steps:
(1) the same as in step (1) of preparation example 1;
(2) the same as in step (2) of preparation example 1;
(3) synthesis of n-octyl alpha-cyanoacrylate
380ml of methanol-formaldehyde solution and 0.95ml of piperidine are added into a 5L three-neck flask provided with a stirrer, a dropping funnel, a condenser and a water separator, 750ml of n-octyl cyanoacetate is added dropwise when the temperature in the flask reaches 40 ℃ or above, and methanol is collected until the internal temperature reaches 120 ℃; then 300ml of petroleum ether is dripped to begin dehydration and accelerate stirring, when the ether water in the reflux water separator is layered and clarified, about 16ml of water is actually collected, and about 300ml of petroleum ether is collected after the water is collected; when the internal temperature reaches 130 ℃, adding 20g of phosphorus pentoxide and 2g of hydroquinone, accelerating the uniform stirring, simultaneously removing the stirrer, the water separator and the dropping funnel, inserting the thermometer and the receiving pipe, connecting the stirrer, the water separator and the dropping funnel with the straight condenser, starting the vacuum pump, removing low-boiling-point substances, continuously adjusting the vacuum degree, changing the receiving bottle when the internal temperature is raised to 150 ℃ after the stirring is stable, and collecting octyl ester crude monomers when the internal temperature is 170-;
(4)4.8 rectification of n-octyl alpha-cyanoacrylate
In a 2L two-mouth flask (containing crude monomer), an air pipe, a fractionating head, a direct type condenser and a receiving bottle are assembled, pressure is reduced, when the vacuum degree reaches-0.1 MPa or below, the temperature is rapidly raised, when the internal temperature is 110-.
Through testing, the preparation example obtains the required n-octyl alpha-cyanoacrylate.
Example 1
The preparation method of the medical adhesive material for rapid hemostasis comprises the following steps:
(1) according to 55 wt%: taking the alpha-n-butyl cyanoacrylate and the alpha-n-octyl cyanoacrylate in a mass ratio of 45 wt%, and fully and uniformly mixing to obtain a medical adhesive matrix for later use;
(2) placing carboxymethyl chitosan in a closed container filled with 1-methylimidazole trifluoroacetate ionic liquid (accounting for 8 wt% of the mass of the carboxymethyl chitosan), removing air, and filling CO in the container2Controlling the temperature and pressure in the closed container to be 80 ℃ and 8MPa to ensure that the CO is filled2The gas is in a supercritical state, and carries the ionic liquid to modify the carboxymethyl chitosan for 10min under the condition that the carboxymethyl chitosan is not in contact with the ionic liquid, the pressure is conventionally released to obtain the modified carboxymethyl chitosan, and the modified carboxymethyl chitosan is dried for standby;
(3) according to the following steps: 10, slowly adding the modified carboxymethyl chitosan into the medical gel matrix, fully stirring until the system is in a gel state, and conventionally sterilizing to obtain the medical gel.
Example 2
The preparation method of the medical adhesive material for rapid hemostasis comprises the following steps:
(1) according to 50 wt%: taking the alpha-n-butyl cyanoacrylate and the alpha-n-octyl cyanoacrylate in a mass ratio of 50 wt% and fully mixing uniformly to obtain a medical adhesive matrix for later use;
(2) placing carboxymethyl chitosan in a closed container filled with 1-methylimidazole trifluoroacetate ionic liquid (accounting for 5 wt% of the mass of the carboxymethyl chitosan), removing air, and filling CO in the container2Controlling the temperature and pressure in the closed container to be 80 ℃ and 8MPa to ensure that the CO is filled2The gas is in a supercritical state, and the carboxymethyl chitosan is not contacted with the ionic liquidCarrying the ionic liquid to carry out modification treatment on the carboxymethyl chitosan for 10min under the condition of (1), conventionally decompressing to obtain the carboxymethyl chitosan to be modified, and drying for later use;
(3) according to the following steps of 3: 10, slowly adding the modified carboxymethyl chitosan into the medical gel matrix, fully stirring until the system is in a gel state, and conventionally sterilizing to obtain the medical gel.
Example 3
The preparation method of the medical adhesive material for rapid hemostasis comprises the following steps:
(1) according to 60 wt%: taking the alpha-n-butyl cyanoacrylate and the alpha-n-octyl cyanoacrylate in a mass ratio of 40 wt% and fully mixing uniformly to obtain a medical adhesive matrix for later use;
(2) placing carboxymethyl chitosan in a closed container filled with 1-methylimidazole trifluoroacetate ionic liquid (accounting for 10 wt% of the mass of the carboxymethyl chitosan), removing air, and filling CO in the container2Controlling the temperature and pressure in the closed container to be 80 ℃ and 8MPa to ensure that the CO is filled2The gas is in a supercritical state, and carries the ionic liquid to modify the carboxymethyl chitosan for 10min under the condition that the carboxymethyl chitosan is not in contact with the ionic liquid, the pressure is conventionally released to obtain the modified carboxymethyl chitosan, and the modified carboxymethyl chitosan is dried for standby;
(3) according to the following steps of 8: 10, slowly adding the modified carboxymethyl chitosan into the medical gel matrix, fully stirring until the system is in a gel state, and conventionally sterilizing to obtain the medical gel.
Comparative example 1
The preparation method of the medical gel material according to the present comparative example is the same as that of example 1, except that the carboxymethyl chitosan is not modified in the step (2).
Comparative example 2
Comparative example a medical gel material was prepared as in example 1, except that the carboxymethyl chitosan was not modified in the step (2) and an equal amount of the ionic liquid was added in the step (3).
Comparative example 3
The medical adhesive material of the comparative example is only alpha-n-butyl cyanoacrylate and alpha-n-octyl cyanoacrylate, and the compounding ratio and the preparation method of the medical adhesive material are the same as those of the example 1.
Examples of the experiments
1. Polymerization Properties
The polymerization performance of the medical adhesive materials prepared in the above examples 1 to 3 and comparative examples 1 to 3 was tested, and the polymerization time of the medical adhesive material was tested, and whether the viscosity performance of the material meets the medical standard was tested, and the test results are shown in table 1 below.
TABLE 1 polymerization Properties of the medical adhesive Material
| Numbering | Polymerization time/s | Viscosity of polymerization |
| Example 1 | 1-2 | Qualified |
| Example 2 | 1-2 | Qualified |
| Example 3 | 1-2 | Qualified |
| Comparative example 1 | 1-3 | Qualified |
| Comparative example 2 | 1-3 | Qualified |
| Comparative example 3 | 1-2 | Qualified |
2. Blood volume adsorption experiment
10mL of each blood sample was placed in a petri dish, and the extent of spreading of the blood was adjusted to concentrate as much as possible in the middle of the petri dish.
Respectively taking 2g of the medical adhesive material prepared in the embodiment 1 and the comparative examples 1-3, spraying and covering the medical adhesive on the surface of the blood ring through a spraying operation, wherein the medical adhesive can be polymerized by itself for 1-3 seconds to form an adhesive film, observing and recording the time (not including the time of film forming and bonding) required by the medical adhesive for adsorbing all blood, and recording the final time when the medical adhesive cannot be adsorbed and does not absorb blood any more, wherein the experimental result is shown in the following table 2.
TABLE 2 blood volume adsorption test results
| Numbering | Whether all are adsorbed | (Total/maximum) adsorption time |
| Example 1 | Is that | 6s |
| Comparative example 1 | Is that | 10s |
| Comparative example 2 | Is that | 12s |
| Comparative example 3 | Whether or not | 9s |
The above data show that the medical adhesive material can realize the hemostatic effect while being bonded by adding the carboxymethyl chitosan with the hemostatic function, and further modify the performance of the carboxymethyl chitosan by selecting the ionic liquid modification mode, so that the hemostatic speed is further improved, the rapid hemostatic effect is realized, and the hemostatic performance of the material is basically not influenced by adding the ionic liquid.
3. Animal hemostasis test
20 rabbits with similar body weight were selected and randomly divided into 4 groups of 5 rabbits, each rabbit was cut off the left ear marginal vein, the right ear marginal artery and two thirds of the left hind limb femoral artery, freely bleeds for 10s, and after 10s, the rabbits were respectively sprayed with the medical adhesive materials prepared in experimental example 1 and comparative examples 1 to 3, and self-formed into films after being pressed for 1 to 2s, and the hemostatic time (including no film-forming adhesion time) in each experimental group was observed and recorded in the following table 2.
TABLE 2 quick hemostasis time results for each experimental group
Therefore, the medical adhesive material can realize rapid hemostasis.
The above embodiments of the present invention are described in detail, and the principle and the implementation of the present invention are explained by applying specific embodiments, and the above description of the embodiments is only used to help understanding the method of the present invention and the core idea thereof; meanwhile, for a person skilled in the art, according to the idea of the present invention, there may be variations in the specific embodiments and the application scope, and in summary, the content of the present specification should not be construed as a limitation to the present invention.
Claims (10)
1. The preparation method of the medical adhesive material for rapidly stopping bleeding is characterized by comprising the following steps:
(1) uniformly mixing alpha-n-butyl cyanoacrylate and alpha-n-octyl cyanoacrylate to obtain a medical adhesive matrix for later use;
(2) placing carboxymethyl chitosan in a sealed container filled with ionic liquid, removing air, and charging CO into the container2Controlling the temperature and pressure in the closed container to make CO2The gas is in a supercritical state, and carries the ionic liquid to modify the carboxymethyl chitosan under the condition that the carboxymethyl chitosan is not in contact with the ionic liquid, so as to obtain the carboxymethyl chitosan to be modified, and the carboxymethyl chitosan is dried for standby;
(3) slowly adding the modified carboxymethyl chitosan into the medical gel matrix, fully stirring until the system is in a gel state, and sterilizing to obtain the medical gel matrix.
2. The method for preparing a medical adhesive material for rapid hemostasis according to claim 1, wherein in the step (1), the mass ratio of the n-butyl α -cyanoacrylate to the n-octyl α -cyanoacrylate is 50-60 wt%: 40-50 wt%.
3. The method for preparing a medical gel material for rapid hemostasis according to claim 1 or 2, wherein in the step (2), the ionic liquid comprises 1-methylimidazole trifluoroacetate.
4. The method for preparing a medical adhesive material for rapid hemostasis according to any one of claims 1 to 3, wherein in the step (2), the ionic liquid is added in an amount of 5 to 10 wt% based on the mass of the carboxymethyl chitosan.
5. The method for preparing a medical adhesive material for rapid hemostasis according to any one of claims 1 to 4, wherein in the step (2), the temperature in the closed container is controlled to be 80-120 ℃ and the pressure is controlled to be 8-10 MP.
6. The method for preparing a medical adhesive material for rapid hemostasis according to any one of claims 1 to 5, wherein the time of the modification treatment step in the step (2) is 5-10 min.
7. The method for preparing a medical adhesive material for rapid hemostasis according to any one of claims 1 to 6, wherein in the step (3), the mass ratio of the modified carboxymethyl chitosan to the medical adhesive matrix is 3 to 8: 10.
8. the method for preparing a medical adhesive material for rapid hemostasis according to any one of claims 1 to 7, wherein the step (3) further comprises a step of adding a functional auxiliary agent.
9. A medical gel material for rapid hemostasis prepared by the method of any one of claims 1-8.
10. Use of a rapid hemostatic medical gel material according to claim 9 for the preparation of a hemostatic material.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113350565A (en) * | 2021-06-11 | 2021-09-07 | 卫纳塞德(北京)医疗科技有限公司 | Medical adhesive material for vessel occlusion and preparation method thereof |
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